More info on the PUP would be good. Also good to know the GVW of the Subaru. The Subaru Outback is not a meaty vehicle and there could be lots of issues.
First let me give you a hint on backing the trailer. Hand on the bottom of the steering wheel and push the wheel in the direction you want the trailer to go. Key on the trailer wheels as the point to start your turns. Don't over-steer. If you aren't in the right position, pull up and try again. We all did it and still do.
Setting up for towing is a huge safety issue. The wrong set-up and you start swaying or bouncing and loose control of the rig.
There are lots of experienced campers on this blog and you will get good advice. Keep asking questions.
If your trailer is not level or if the tail of the tow vehicle (TV) sags then the tongue is too heavy. A load-leveling hitch can solve that problem. And it really works.
Make sure the trailer brakes work (if equipped)as that little TV is going to be tested even with good working brakes. Brake early - early - early.
A trany cooler is a big job. If you are not going that far or more importantly into the mountains then just take it easy on the acceleration.
Destinations on purpose: Canada: Alberta, BC, Nove Scotia, PEI, New Brunswick. USA: ME,NH,MA,VT,NY,MT,WY,MN,MI,WI,GA,VA,FL,UT,CA,OR,ID,CO,NV,AZ
:BLife is Good
2009 Jayco 1206
2011 Toyota Tundra